How to Woo Felicity Smoak
by pameblina
Summary: When Oliver realizes he'd like to date Felicity he finds she's not quite as receptive as he expected. A 3-parter telling the story of how he "woos" her. Only my second fanfic ever, but ya'll have been so nice so I kept writing! I have no beta, all mistakes are mine.
1. Chapter 1

How to Woo Felicity Smoak  
by pambelina

Chapter One

The first thing Oliver heard when he entered the basement was Diggle apologizing. Then came Felicity's quick response, "No, you're doing great, just relax a little more."

Oliver followed the voices and found the two of them in workout clothes standing on the mats. Dig had a hand on Felicity's hip and his other hand held hers. Some Frank Sinatra played from somewhere.

"Don't look at your feet," Felicity said. "Look at me."

Dig took a wrong step and crushed her foot. Oliver snickered. They noticed him for the first time. Felicity gave him a stern look and shushed him. Dig raised an eyebrow, daring him to laugh again.

Oliver raised his hands in surrender, folded his arms, and sat down on the edge of Felicity's desk to watch.

"Okay so one of your biggest problems in dancing is a strength in fighting," Felicity explained. "You need to let your partner know what your next move will be, which, of course, you don't want to do when you fight."

Dig nodded. "How do I do that?"

"Pushing your hand forward, or raising your knee just before you take a step, or by putting pressure on my back." Felicity pointed to each place as she explained. "That means your hand needs to actually be on my back though."

It might have been the first time Oliver had ever seen Dig blush.

"What's wrong?" she asked.

"Nothing," Dig hurried to say. "You're just not wearing a lot, so my hand would be resting on…"

"My skin?" Felicity gave a laugh. "Who knew you were such a prude!"

Oliver laughed with her and Dig smiled good-naturedly. "Okay, that's enough. You can both shut up now."

"Do you want me to run and change? I can."

"It's fine, let's just do this." Dig placed his large hand on her lower back.

It was then that Oliver fully took in what Felicity was wearing. A fuchsia sports bra and short black workout pants that only just covered the curve of her butt. With each step she took her hips moved and Oliver found himself nearly hypnotized by her swaying posterior.

He'd never once held her as close as Dig was now. Well once, but they were swinging over a huge drop, not moving together like that. He imagined his hand where Dig's was on her pale back, pinky finger on the waistband of her little shorts. So easy to just…

"Why are you guys doing this, anyway?" Oliver practically yelled.

The two paused to stare at him.

"Carly asked Dig to be her date for a wedding."

"Where there will be dancing," Dig added.

"So I offered to share my limited knowledge with him so he can wow her on the dance floor." Felicity smiled. "Few things are sexier than a man who can dance."

Oliver, once again, thought about showing her his dance moves.

"I'll settle for not stepping on her feet," Dig said.

"You're doing great! One or two more lessons and you'll be a pro."

Dig looked at his watch. "Those lessons will have to wait, unfortunately. I'm meeting Carly for dinner." He headed to the bathroom to shower and change.

Felicity turned to Oliver. "I saw you smirking. You think you can do better?"

He stood up. "Oh, I know I could."

"Mr. Queen, I'm afraid you'll have to prove it." She held a hand out to him.

The thoughts he'd been having about her came back in a rush. "Maybe another time."

"I dare you."

"Are you serious?" He took a step toward her. "What are we, six?"

"I double dare you." She smiled with her tongue between her teeth.

Desire ruled sense and he stepped onto the mat. "I've done worse things on a dare."

"I have no doubt."

Oliver took her outstretched hand and reveled in the moment when his other hand touched the soft skin of her bare back.

"Oh wait." Felicity pulled back a step, reached into her sports bra, and pulled out her phone. "Music."

Though trying to be a gentleman, Oliver failed, and stared at her chest as she put the cell back in place.

"Hey, my eyes are up here," she teased when she caught him looking.

The song started and he bobbed his head to catch the rhythm before he led her in the first few steps.

"Wow," Felicity said. "You weren't kidding. You do know what you're doing."

"I took a ballroom dance class."

She laughed so loud it rang through the rafters. "Seriously?"

Oliver smirked. "Great place to meet chicks."

"Of course that was your motivation."

He spun her around and pulled her back flush against him. "Some women think guys who can dance are sexy."

Felicity swallowed. "So I've heard."

The next time he spun her he dipped her. She threw her head back, exposing that long gorgeous neck of hers. He couldn't resist, he leaned over and kissed it.

When he pulled her back up he expected a reaction of some kind, but she acted as if nothing out of the ordinary had happened. Something about their dance was showing off her confidence, a side of her he'd never seen before, but wanted to see again and again. He wanted to see every side of her and learn everything there was to know about her. Every last thing.

He could tell the song was about to end, so he spun her one last time. This time, when he pulled her in Felicity swung her leg up so her knee was on his hip, her leg wrapped around him. Instinctively he put his hand on her thigh. She'd thrown her arms over his shoulder and the two of them were closer than they'd ever been before.

It would take absolutely no effort at all to lean down and kiss her. Suddenly the most interesting question in the world was _What does Felicity Smoak taste like?_ He stared at her bright pink lips, then back at her eyes. She was so calm. A little breathless, but that was probably from the dancing, not their proximity.

The bathroom door opened. Felicity tried to pull away, but Oliver held her tight. Her eyes went wide and she finally looked as frazzled as he felt.

Dig didn't even react to seeing them that way. "I'll be with Carly, call if you need me." He stopped halfway up the stairs. "Try not to need me."

"Bye, Dig." His voice was so soft he doubted he'd been heard.

Felicity slid her hands from his shoulders to his chest and pushed away. "Night. Tell Carly I said hi."

Oliver followed her with his eyes, watching her bend over to pick up her clothes. "What are you doing tonight?"

"Not you."

He waited for the embarrassed rambling that usually followed statements like that, but none came. She looked at him with an arched brow.

"You have a tendency, I've observed, to jump into bed with a woman and worry about the consequences later."

He put his hands in his pockets, not disagreeing with her.

"Oliver, you've been thinking of me for about five minutes. I've been thinking of you since the day we met." She held her clothes tight to her chest. "I'm not a one night stand."

That hurt. "I'm not starting anything I'm not prepared to finish."

Felicity looked disappointed in him. "I don't want to be a girl you _finish_ with."

He walked over to her. "That's not what I meant. I'm not walking into this blindly. I know what I'm doing. I know what I want."

"Do you? That's a first." She moved toward the bathroom. "You don't know the first thing about wooing a girl like me."

"Wooing?"

She smiled. "Yup."

"Sounds like a challenge, Felicity."

She shook her head and kept walking.

"Challenge accepted!"

Now, how did one go about _wooing _Felicity Smoak?


	2. Chapter 2

Chapter Two

Felicity had been running early all morning and decided to take advantage of it. If she got to work a half hour early then she could leave that much earlier… and get to the Foundry earlier.

Last night she'd danced with Oliver and it had been one of the most romantic moments of her life. Although his time on the island had definitely changed him in significant ways, she wasn't so sure it had changed his ways with women.

She was wary about starting something with him, but not an idiot. Or maybe she was an idiot. Either way she wanted to see him again as soon as possible.

She had a swing in her hips when she exited the elevator on her floor at Queen Consolidated.

"Morning, Cho!" she greeted her supervisor with an enthusiastic wave.

The short woman put a hand on Felicity's arm. "Is it your birthday?"

She shook her head. "Why?"

Cho gave a knowing smile. "Secret admirer then? So much better."

"What are you talking about?"

"You'll see." She winked and walked away.

"What the…?"

When Felicity got to her desk she saw exactly what Cho had been talking about. An enormous vase of yellow daisies sat next to her keyboard. She knew he had sent them without looking at the card, but she pulled it out anyway.

**Trying to figure out your favorite.  
O**

It was written in his neat square hand, meaning he had gone to the flower shop in person. It wasn't even 8am, when could he have done that?

**Do you own a florist?** She texted him.

Her phone pinged seconds later. He had been waiting for her call, apparently.

**Kind of. Was I close?**

She smiled and bit her bottom lip. **Common assumption, but nope. Wrong flower. Wrong color.**

**I guess I'll have to try again.**

**Looks that way.**

She put her phone away. It would be fun getting flowers every once in a while until he figured out her favorite.

At five to nine she pulled herself away from her computers to go to the weekly IT staff meeting. Walking down the hall she saw someone exit the elevator with an enormous bouquet of orange roses. Her steps faltered and she couldn't help but turn and follow him.

Sur enough he put the bouquet next to the vase of daisies. She smiled wanly at the guy and picked up the card.

**How about now?  
O**

She didn't text him immediately. Instead she went to her staff meeting, pretended to listen, but spent the time thinking about Oliver. Was he really going to keep sending her flowers all day until he got the right ones? Tomorrow too? And maybe the next day?

When the meeting ended she texted him.

**Wrong again. Will all the bouquets be this big?**

Her phone pinged. **Yes.**

**Please remember I drive a Mini.**

**Give me a hint then.**

Felicity tapped her pen against her lips and thought for a second. **The flower name is also a movie name. **She hoped that hint wasn't too obvious.

An hour later a bouquet of gorgeous pinkish-purple magnolias came through her office door.

**Nope.**

**I thought Steel Magnolias might be a stretch.**

She smiled. **Another hint?**

**Please!**

**It's also the name of a city not in USA.**

It was nearly lunchtime before the next bouquet came.

"You're not the usual flower delivery boy." Felicity stood up. "Take up a part time job?"

Oliver shook his head and grinned. "I wanted to give you these in person."

"Why?"

"Because I know I got it right this time."

She smirked. "Really? After only 3 other tries? How do you know?"

"I cheated," he said sheepishly. "I asked our florist for help."

Then he pulled the bouquet from behind his back: a simple arrangement of Casablanca lilies tied in a dark green ribbon.

"Oh…" she breathed, as she took the flowers from him. "They're perfect. No one's ever bought them for me before. Oliver…"

She looked up to find him standing right in front of her.

"Felicity," he whispered. "Can I kiss you?"

It was one of the most difficult words she'd ever said. "No."

He looked deflated.

"Not yet, but you can take me to lunch."

"Sounds perfect." He gave her that smile that always made her knees weak.

She put the lilies in some water and grabbed her purse.

"Where do you want to eat?" Oliver asked, taking her hand.

There was a moment of panic when she was scared of what she was doing. There was no way that Oliver would be interested in her for long. But maybe she should just enjoy it while it lasted. So she leaned into his arm, reveling in their closeness. "I'm kind of in the mood for Mexican."

"I know the perfect place."

"I'm sure you do." She laughed. "Can we make it in and out of there in an hour?"

"Mr. Queen." Cho greeted him. "Taking Felicity to lunch?"

"Mrs. Cho." He gave her a friendly nod. "Yes, but I'm not sure we'll be able to make it back in only an hour."

Felicity squeaked. "He's joking! I'll definitely be back well before –"

Cho raised her hand to stop the inevitable ramble, but didn't take her eyes off of Oliver. "I seem to recall giving her the rest of the day off. She must have forgotten."

"Thanks Cho," she said quietly.

The woman leaned close to her. "No one deserves it like you do." Then she turned her stern supervisor look on Oliver, the one Felicity always dreaded getting. "Treat her well, Mr. Queen."

Oliver actually looked nervous. "No one values Felicity's brains or beauty like I do, ma'am."

Cho didn't drop the look. "See that it stays that way."

"I never realized how scary she is," Oliver said when they were safely in the elevator.

Felicity laughed. "Do you mind if we stop by my apartment before lunch?"

"Sure, why?"

"I want to change."

"You look amazing." Oliver put his arm around her.

"Thanks, but I want to get out of my work clothes. If the rest of the day is for fun then I want to be in play clothes."

"Play clothes? So is this a play date?"

Felicity blushed. "You know what I mean. I want to be in comfy clothes."

"I'd love to see your apartment."

Suddenly she pictured the huge mess it was. "Never mind, I'm starved. Let's just go to lunch."

#

Somehow Oliver was able to convince her to go to her apartment anyway. Something he was incredibly proud of. He wanted her to be comfortable for their afternoon together, but he was also selfishly dying to see where she lived.

At her apartment door Felicity turned to him. "Is there anything I can say to convince you to stay out here?"

Oliver tried not to be hurt. "You don't trust me in your apartment?"

"It's just that it's a huge mess right now. Not all of us have maids and I work a lot. At two jobs. Both for you and yours, I might add. I can't let you see it this way." She chewed her bottom lip as she pleaded with him.

"If you don't trust me not to judge you for a few dirty dishes, then I'll wait here in the hall."

"Well, when you put it that way…" She unlocked the door and invited him in with a wave of her hand. "I tried to warn you."

Felicity excused herself to change and Oliver had the freedom to explore. Her place was bright and cluttered, just how he imagined the inside of her mind would be. There was so much to look at he couldn't decide where to start.

The enormous wall of books seemed as good a place as any.

One entire bookshelf was filled with manuals and non-fiction books on computers, different theories in math, etc. The next bookshelf was infinitely more interesting to him. He looked over the titles carefully until he noticed something.

"Felicity?"

He heard a muffled "Yeah?" from her bedroom.

"Why do you have so many copies of the same books?"

The door squeaked and she came out, looking even more beautiful than before in a black and white striped shirt, bright red pants cuffed at the bottom and a pair of aqua blue flats. Her hair was out of its usual pony tail, hanging loose over her shoulders, and her lips were bright red.

Bright kissable red.

"What?" she asked.

"What?" Oliver repeated, coming out of his fantasy.

"What did you ask? I didn't hear you."

"Oh, the books. I noticed you have five or six copies of the same ones and I just wondered about their significance."

Felicity walked over to the bookshelf as she put on a pair of aqua blue earrings. "It started my freshman year of college. I was pretty out of my element so I revisited one of my favorite childhood stories."

"_Alice in Wonderland_."

"Yup. And it made me feel better. So then every time I saw a copy somewhere I would buy it. I always had one with me, for almost the whole year." She picked up an especially battered paperback version and rubbed the cover lovingly. "Then it just became a thing. I'd find a book that spoke to me and I'd buy up copies."

He'd never heard of anyone doing something like that. "You're incredible." She blushed. "What's the book right now?"

"Oh." Her face went redder. "_Jane Eyre_."

"Haven't read it. What's it about?" Oliver loved her blushing.

"Um, a really plain-looking but smart orphan goes to work for a rich, good-looking, broody man with a secret."

"Hmm." Oliver played dumb. "Why would that particular book speak to you right now?"

A knock at the door saved her from answering.

"Oliver?" she asked as three flower delivery people, all carrying huge vases of Casablanca lilies came in.

"Hope you don't mind, I donated the wrong flowers to the children's hospital and had these delivered so you'd have some at work and some at home." Oliver handed each of them a $20 and closed the door after them.

Felicity wasn't smiling.

"What's wrong?"

"Why are you doing this?" Her body language was completely shutting her off from him.

He couldn't understand her sudden mood swing. "I'm wooing you."

"Why?"

"What do you mean _why_?"

"I need to know, Oliver. Because with you I have a great potential for heartbreak, so you need to tell me the truth. For my heart's sake. Is it because I told you no? Am I some sort of a conquest now? A challenge? Are you only trying to get the ungettable?" Her tone slowly rose. "What happens when I finally say yes? How long before the novelty wears off and you're done with me?"

"Felicity." He took a step forward, but she moved out of his reach. "You're not a conquest."

She huffed.

"You are a challenge though. Because there has never been another girl like you and I'm working my ass off trying to make myself good enough for you." He took in a shaky breath. "I don't think I ever will be, but I will never stop trying. And I'm hoping you're generous enough to overlook the gap between who I am and who I'm trying to be."

Out of nowhere Felicity launched herself into his arms and kissed him. He was unprepared for the ferocity of her kiss. He wrapped his arms around her, lifted her off the ground and kissed her with everything he had. With that one kiss he tried to tell her all the things he didn't have words for, all the things he liked about her, and all the things he still wanted to learn.

After what seemed like forever but not nearly long enough at the same time, Felicity pulled away.

"Strawberries," Oliver said, setting her back on the ground.

"Excuse me?"

He touched his forehead to hers. "Your lips taste like strawberries."

Felicity breathed heavily. "Lunch. We need to go to lunch. Right now."

"Why?" He pulled her closer.

"Because if we don't leave right now then I just might pounce you."

Oliver let out a surprised laugh. "_Pounce_ me?"

She nodded and put a little more space between them.

"That sounds pretty great, actually."

"I know," she said. "And it will be, but I'm not ready for that yet. I still worry that you…"

"You don't trust me yet?" The truth stung.

She shook her head, nodded, then shrugged. "I do, but I don't. I… my heart is really fragile."

"At the risk of sounding cheesy, I promise I'll handle with care."

Felicity gave him a desperate look.

"Having said that, let's go to lunch." She looked relieved at his words. "And you can tell me more about _Jane Eyre_."


	3. Chapter 3

Chapter Three

"I figured you for a cat person," Oliver said as they pulled up to the restaurant.

"Bite your tongue, infidel!" Felicity laughed. "I don't trust cats, they're creepy. I always feel like they're plotting to kill me." She turned off the engine and hopped out of the car.

"So why don't you get a dog?" He reached for her hand.

"You've seen how small my place is." She laced her fingers through his.

"So get a small dog."

"They scare me. I only like big dogs."

Oliver laughed. "How can little dogs scare you?"

Before she had a chance to answer the hostess greeted them. "Oliver Queen," she said in a way that suggested she knew him.

Felicity looked at Oliver.

He forced a smile. "How are you, Vanessa?"

"Veronica." She bit her lip suggestively. "Not as good as the last time I saw you, that's for sure."

Felicity stared at her shoes, wishing she were anywhere but there.

"Table for two, please." Oliver squeezed her hand.

"Only two?" Veronica asked. Felicity could feel her appraising gaze. "This way."

They hadn't taken more than five steps into the dining room before two girls stopped them.

"Oh my hell, Ollie Queen!" The short brunette squealed. "We were just talking about you!"

"We totally were!" The tall brunette added helpfully.

"We were rating the guys we've slept with and you made both of our top five! Can you believe it?"

Felicity walked away before she could hear anymore. Veronica was waiting patiently by their table.

"So is this a business lunch?" she asked pointedly.

"Yup," Felicity said. "Because Oliver would never date a girl like me, right?"

Veronica handed her a menu. "Your waitress will be right over."

"Oh good! Has he slept with her too?"

Veronica had enough brains not to respond and made a hasty retreat. Moments later, Oliver sat down across from her.

"Sorry about that." He tucked his napkin into his lap. "Why'd you just leave me with them?"

Felicity didn't look up from the menu. "I thought you might want to catch up."

"With them? I don't even remember their names."

She gripped the menu so hard she was afraid she might rip it, laminated or not. "Well this is kind of a dive compared to what you're used to. I wouldn't expect you to remember all the trysts where you slummed with middle-class girls."

The waitress arrived just in time to save Felicity from hearing his response.

"We need a minute," Oliver said.

"I don't. I know exactly what I want." She hurried and gave her order. "Now, if you'll excuse me, I have to pee."

She left before Oliver or the waitress could say anything. In the bathroom she paced the floor, warring with the two voices in her head.

The first voice was reminding her of all her flaws and telling her a man like Oliver could never be with a nerd like her. That voice sounded a lot like Prissy Wells, the most popular girl when she was in high school.

The second voice listed all the reasons she was too good for Oliver and why she was an idiot to be on this date in the first place since he'd only break her heart. That voice was her best friend Eliza.

It took a lot of concentration, but she pushed both voices away until she only heard a third voice – her own.

Oliver rose when she came back to the table. "I was afraid you'd climbed out the window."

"I wanted to, but there wasn't one." Felicity picked up her fork and started eating. She couldn't believe she'd been gone long enough for the food to arrive.

"Felicity, listen –"

"No, let me talk. In the first five minutes of our date we ran into three people that you've slept with. Three!" She held up her fingers to emphasize the point. "Now, although it would be nearly impossible, how would you feel if that happened to you? How would you feel if we ran into three guys I'd slept with, one right after the other?"

He stared at his plate. "I wouldn't like it."

"And you'd probably compare yourself to them to see how you measured up, right?"

Oliver shrugged and nodded.

"Well that's what I did." She struggled to reign in her emotions. "And do you know how I rate compared to them?"

"No contest."

"Exactly." There were tears threatening, but her anger held them back.

He met her eye. "No contest because none of them are you. None of them are even close to you. They were all before the island. The Oliver today wouldn't look twice at any of them, much less sleep with them. There's only one girl I want and that's you."

"Well." Felicity stabbed at her food. "I guess I wouldn't want you to judge me based on decisions I made six or seven years ago."

"So we're okay?" he asked, hopeful.

"We're okay." She looked up at him and sighed. "I know this will happen again though. I can't promise I won't be a little jealous when it does."

Oliver grinned. "I think you're hot when you're jealous."

She couldn't help but smile. "Wait until it happens to you."

"So, small dogs."

The abrupt subject change surprised her. "What?"

"Why are you afraid of them?" he asked.

"They're yappy and mean. Big dogs, in my experience, are sweet and gentle. The only time I was ever bitten was by a small dog." She showed him the almost invisible scar on the back of her hand. "Besides the space issue though, I couldn't really afford a dog right now."

"I could buy you one," Oliver said. "It could even live at the mansion until you get a bigger place."

"Are you going to buy that for me too?"

"Sure."

She put her fork down. "That's something I wanted to talk to you about. You don't have to spend money on me."

"What do you mean?"

"I mean the flowers today probably cost a small fortune. And when I told you about _Jane Eyre_ I could practically hear you thinking about where you could buy me a rare edition."

Oliver nodded sheepishly.

"I don't need any of that. I'm not dating you for your money."

"We're dating then?" He grinned.

Felicity smirked. "If I say yes are you going to stop wooing me?"

"Never."

"Okay, then we're dating."

#

They left the restaurant hand in hand, both grinning like idiots. Oliver couldn't remember ever being this happy. Suddenly Felicity dropped his hand, yelled "Johnny!" and ran to hug a guy he'd never seen before.

The guy picked her up off the ground and spun her around. Felicity squealed.

"Put me down, you dork!" She laughed. When he finally put her down she kept a hand on his arm. "Oliver, this is Johnny. Johnny, this is Oliver."

Oliver shook his hand, resisting the urge to break it. "Nice to meet you, Johnny."

"Same here. So how do you know Felicity?"

"We work together," Felicity said.

"And we're dating." Oliver slung a possessive arm over her shoulder. "How do you two know each other?"

"We're practically family," Johnny said, beginning to seem a little possessive himself. "I'm married to her best friend, Eliza."

Oliver immediately relaxed. "We'll have to meet up for dinner some night."

Felicity clapped. "That would be so much fun. I haven't seen you guys in ages. I'll text Eliza and work out the details."

"Okay." Johnny smiled. "She'll probably want to do it at our place. Threaten Oliver on home turf."

He and Felicity said goodbye and Johnny walked away.

"Why is Eliza going to threaten me?" he asked.

"Because we're dating and that's what she does. She'll threaten to lop off your balls if you hurt me."

"Lop off my balls?" He opened the driver's side door of her Mini for her.

"Or something akin to it." Felicity shrugged. "By the way, was that jealous Oliver I just witnessed?"

"What?" he scoffed. "No."

"Really? Well, if that's the case, I'd hate to see you when you are jealous."

He closed her door and got in on the other side. "Hypothetically, if I were jealous, I would have every right to be."

"How do you figure?"

"Some random guy was hugging my girlfriend."

"Girlfriend," Felicity repeated. "I'm Oliver Queen's girlfriend."

"How does it feel?" he asked.

"Good. How do you feel about being Felicity Smoak's boyfriend?"

"It feels pretty nice." He tried to hide his smile. "I just wish she would have wooed me more. It's embarrassing how easy it was for her to get me."

"Really?" Felicity bit the side of her cheek trying not to smile. "How does a girl go about wooing Oliver Queen?"

"That's for you to figure out."

"Challenge accepted," Felicity said with a laugh.


End file.
